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Potassium Hydroxide → 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoic acid

HRID 1786049
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HRID 1786049 반응식
[C:1]([N:4]([C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:35]=[CH:34][C:20]([O:21][CH2:22][CH2:23][CH:24]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[C:25]([O:27]C)=[O:26])=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:36])[CH2:6]1)(=[O:3])[CH3:2].[OH-].[K+]>O1CCCC1.CO>[C:1]([N:4]([C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:35]=[CH:34][C:20]([O:21][CH2:22][CH2:23][CH:24]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[C:25]([OH:27])=[O:26])=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:36])[CH2:6]1)(=[O:3])[CH3:2]
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HCID 14797Potassium HydroxideHCID 68920582methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydro-quinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoate

생성물 1

HCID 575955164-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoic acid수율 55%

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran
용매

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온도
50 °C

실험 절차

Methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydro-quinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoate was hydrolyzed to the acid by dissolving in 6 ml tetrahydrofuran/methanol (1/1) and potassium hydroxide (0.04 g in 2 ml water) was added. The mixture was heated to 50° C. for 18 hours. The mixture was cooled to room temperature and concentrated. Then neutralized with 1M HCl and extracted with dichloromethane. The dichloromethane solution was dried and concentrated. The residue was purified by silica gel chromatography (87% CH2Cl2/13% methanol) to afford 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoic acid (0.04 g, 55%).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated
  3. extractionextracted with dichloromethane
  4. dry with materialThe dichloromethane solution was dried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (87% CH2Cl2/13% methanol)

출처 및 근거

ORD 기록
ord-41a7afebb8de40dc819fe91dbbc286c1
출처 데이터셋
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07504508B2

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